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ChemInform Abstract: Ring Expansion of 2-Alkylidenedihydroquinolines to 2-Iminodihydro-1-benzazepines by Phenyl, Methanesulfonyl, and Trifluoromethanesulfonyl Azide.

โœ Scribed by Helmut Quast; Svetlana Ivanova; Eva-Maria Peters; Karl Peters

Book ID
101891069
Publisher
John Wiley and Sons
Year
2010
Weight
40 KB
Volume
31
Category
Article
ISSN
0931-7597

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2-Alkyl-1-methylquinolinium hexafluorophosphates 1 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinolines 2, which are investigated by NMR spectroscopy. 1,3-Dipolar cycloaddition of phenyl azide to 2 yields the spirocyclic products 10. While, at 80ฯช110 ยฐ

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2-Alkyl-1-methylquinazolinium hexafluorophosphates 9 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinazolines 10, which were investigated by NMR spectroscopy. Trapping with methanesulfonyl azide (5a) of 10 in situ or subsequent treatment with trifluorome